Tetrahydrofuran → HCID 10766034, compound

HRID 346229Notes

Reaction equation

HRID 346229 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[C:6]2[C:11]=1[C:10](=[O:12])[C:9]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[C:6]2[C:11]=1[CH:10]([OH:12])[C:9]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 10575517HCID 10575517, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10766034HCID 10766034, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 8-chloro-2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone (180 mg) in freshly distilled tetrahydrofuran (5 ml) was added lithium aluminum hydride (15 mg) with stirring in an ice bath under nitrogen and the mixture was stirred for 15 minutes in an ice bath. To the mixture was carefully added aqueous saturated ammonium chloride solution (5 ml) in an ice bath, and then diethylether (10 ml) was added thereto The separated aqueous layer was extracted two times with diethyl ether and the combined organic layers were washed with brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the oily residue which was crystallized from diisopropyl ether to yield 8-chloro-2,2-dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol (142 mg).

Workup

  1. stirringthe mixture was stirred for 15 minutes in an ice bath
  2. extractionThe separated aqueous layer was extracted two times with diethyl ether
  3. washthe combined organic layers were washed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the oily residue which
  7. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-4300cf9ef816449cb35c07da60a8a9cd
Source dataset
uspto-grants-1991_10
Patent number
US05061718

Reaction notes

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